Belaam said:
I don't really rate the war ones as hilarious as they led to a lot of death (likewise any that may go up involving people holding evidence-free religious beliefs). However, I'll stick with the military theme that has developed from the OP
Either the oil embargo against Japan in 1941 or Japan's raid on Pearl Harbor (neither went well).
Situation: The U.S. started an oil embargo against Japan (which got 80% of its oil from the U.S.) to force them out of China and do what the U.S. wanted.
How the U.S. screwed up: Japan realized that if they attacked any neighboring countries with oil, the U.S. would attack them, so they decided to take out the U.S.'s fleet all at once. Which they were able to do reasonably easily as the U.S. conveniently put most of their navy in the same place.
Actually, The Admiral in charge of the operation considered it a failure because not a single aircraft carrier was sunk. In the end, he was right.
Situation: Suffering from a lack of oil, Japan takes out the U.S.'s Navy and hopes to gain oil supplies before the U.S. rebuilds its fleet.
How Japan screwed up: The U.S. rebuilt much faster than expected, getting oil supplies took longer, and, you know, atomic weapons.
Actually, those three are unrelated. The atomic weapons were already in development before the attack on Pearl Harbor.
The U.S. had thousands of people capable of working, looking for work, that couldn't get jobs because of the economy. When the government said "Build this!" the American people said, "For Freedom" and the economy spooled up to build everything it would need to take over a continent. Of course, with no one knowing what the Americans were capable of building because half our workforce wasn't working, we spooled up for war even faster than our own allies thought we would.
As for the problem with conquering China for their oil:
no plan of operations extends with any certainty beyond the first contact with the main hostile force. [http://en.wikiquote.org/wiki/Helmuth_von_Moltke_the_Elder]
That is a quote by a German military commander. The Axis should have known better.
Really, any player of the Civ games could have predicted these screw ups: if you make demands of a country that can't fulfill the demands OR if you attack a more developed country to get its supply nodes and fail, you're going to pay for it.
Really? Anyone from that era who played Civ games would have known better? Where do you think the creators of Civ got their pre-programmed responses from?
You are mistaking hindsight with common sense.